Potassium Carbonate → HCID 59016049, compound

HRID 968822Notes

Reaction equation

HRID 968822 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]2[N:12]([CH3:17])[C:13](=[O:16])[NH:14][N:15]=2)=[CH:4][CH:3]=1.[O:18]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:33](=[O:36])([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:17][N:12]1[C:11]([CH2:10][CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:28][C:27]3[CH:30]=[CH:31][CH:32]=[C:25]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:26]=3)=[CH:7][CH:6]=2)=[N:15][N:14]([CH2:28][C:27]2[CH:26]=[CH:25][CH:32]=[C:31]([O:36][C:33]3[CH:21]=[CH:20][CH:19]=[CH:24][CH:23]=3)[CH:30]=2)[C:13]1=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 932913-Phenoxybenzyl chlorideHCID 59015953HCID 59015953, compound

Product 1

HCID 59016049HCID 59016049, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[3-(4-hydroxyphenyl)propyl]-4-methyl-2,4-dihydro-[1,2,4]triazol-3-one (Example 1, step C) (0.350 g, 1.50 mmol) in DMF (5 mL), was added 3-phenoxybenzyl chloride (0.94 g, 4.29 mmol) followed by potassium carbonate powder (0.74 g, 5.35 mmol). The mixture was stirred at rt under nitrogen overnight. The reaction mixture was partitioned between ethyl acetate (20 mL) and water (20 mL). The organic phase was dried over MgSO4 and filtered. Evaporation of solvent gave a crude product, which was purified on a silica gel column (125 mL SiO2) eluting with 50% EtOAc/hexanes to give the titled compound as colorless oil (0.0.78 g, 87%). 400 MHz 1H NMR (CDCl3) δ 7.32 (q, J=7.6 Hz, 4H), 7.30−7.25 (m, 3H), 7.20−6.90 (m, 10H), 6.97 (d, J=8.8 Hz, 2H), 6.87 (d, J=8.8 Hz, 2H), 5.01 (s, 2H), 4.91 (s, 2H), 3.16 (s, 3H), 2.63 (t, J=7.2 Hz, 2H), 2.46 (t, J=7.6 Hz, 2H), 1.94 (quintet, J=7.6 Hz, 2H); Mass (M+H+)=598.4.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (20 mL) and water (20 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customEvaporation of solvent
  5. customgave a crude product, which
  6. customwas purified on a silica gel column (125 mL SiO2)
  7. washeluting with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-04d7ca1fcc164abbafd718cc5c449cb7
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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